CN101821341A - Tinting pigment through modification - Google Patents
Tinting pigment through modification Download PDFInfo
- Publication number
- CN101821341A CN101821341A CN200880110951A CN200880110951A CN101821341A CN 101821341 A CN101821341 A CN 101821341A CN 200880110951 A CN200880110951 A CN 200880110951A CN 200880110951 A CN200880110951 A CN 200880110951A CN 101821341 A CN101821341 A CN 101821341A
- Authority
- CN
- China
- Prior art keywords
- pigment
- tinting pigment
- modification
- tinting
- singly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0001—Post-treatment of organic pigments or dyes
- C09B67/0004—Coated particulate pigments or dyes
- C09B67/0008—Coated particulate pigments or dyes with organic coatings
- C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
- C09B67/0085—Non common dispersing agents
- C09B67/009—Non common dispersing agents polymeric dispersing agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/20—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the process features
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/41—Polymers attached to the pigment surface
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/42—Ionic groups, e.g. free acid
- C09B68/425—Anionic groups
- C09B68/4257—Carboxylic acid groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/441—Sulfonic acid derivatives, e.g. sulfonic acid amides or sulfonic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/443—Carboxylic acid derivatives, e.g. carboxylic acid amides, carboxylic acid esters or CN groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
- C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
- C09B68/446—Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/108—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a phthalocyanine dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
The present invention relates to comprise the tinting pigment through modification of the tinting pigment that is connected with organic group.Described organic group is connected with described tinting pigment via at least one carbon atom of C-C singly-bound or two keys, and wherein said C-C singly-bound or two key are not the parts of aromatic systems.Described organic group further comprises at least one active group at least one carbon atom of described C-C singly-bound or two keys.The invention also discloses the method for preparation through the tinting pigment of modification, and comprise through the moisture and nonaqueous dispersion of the tinting pigment of modification, for example jetted ink.
Description
Technical field
The present invention relates to through the tinting pigment of modification and comprise these dispersion and inkjet ink compositions through the tinting pigment of modification.
Background technology
Tinting pigment (colored pigment) product through modification is known in the various application.For example, known various organic group with improve the dispersiveness of described pigment in liquid carrier (vehicle) (for example, water-bearing media) being connected of tinting pigment.The dispersiveness of such improvement has advantageously promoted the uniform distribution of described tinting pigment in the whole composition of studying.
People's such as Johnson U.S. Patent No. 5,837,045 and 5,922,118 disclose the tinting pigment through modification of the organic group with at least one connection, and wherein said organic group comprises (i) at least one aryl or C
1～C
12Alkyl and (ii) at least one ionic group or can Ionized group.The Johnson patent further discloses aqueous dispersion and the nonaqueous dispersion that contains the described tinting pigment through modification that is suitable for multiple application (for example, comprising printing ink, toning agent, paint, tackiness agent, coating and plastics).The Johnson patent also discloses the method for preparing above-mentioned tinting pigment through modification.
U.S. Patent No. 6,660,075 discloses the carbon black that is connected with organic group, and wherein said organic group is connected with carbon black by one or two carbon atom of C-C singly-bound or two keys, and described C-C singly-bound or two key are not the parts of aromatic systems.The purposes of described carbon black in filler, reinforcing filler, UV stablizer, graphitized carbon black or pigment also disclosed.
Though the tinting pigment through modification can be used for for example being used for jetted ink in the various application, still need to have further improvement performance characteristics through modified pigment, thereby the previous favourable alternative through modified pigment is provided.
Summary of the invention
The present invention relates to have the tinting pigment through modification of the organic group of at least one connection.Described organic group is connected with described tinting pigment via at least one carbon atom of C-C singly-bound or two keys, and described C-C singly-bound or two key are not the parts of aromatic systems.Described organic group further comprises at least one active group (activating group) at least one carbon atom of described C-C singly-bound or two keys.Described tinting pigment can be the pigment dyestuff of any type and does not comprise charcoal blacks.Preferred pigment comprises phthalocyanine blue and quinacridone.
The invention further relates to the aqueous dispersion and the nonaqueous dispersion that comprise liquid carrier and above-mentioned tinting pigment through modification.Such dispersion can be used in any basically suitable composition, and described composition for example comprises plastics, rubber, paper, fabric, coating, paint, toning agent, tackiness agent, latex and printing ink.
Foregoing has quite broadly been summarized feature of the present invention, makes to understand following specific descriptions preferably.To additional features of the present invention and the advantage that form claim theme of the present invention be described hereinafter.It is exemplary and explanat should be understood that above-mentioned general description and the following specifically describes the both, and intention is to provide of the present invention the further specifying to claimed.
Embodiment
The present invention relates to have the tinting pigment through modification of the organic group of at least one connection.Described organic group is connected with described tinting pigment via at least one carbon atom of C-C singly-bound or two keys, and wherein said C-C singly-bound or two key are not the parts of aromatic systems.Described organic group further comprises at least one active group at least one carbon atom of described C-C singly-bound or two keys.
Term tinting pigment used herein is meant any organic coloring pigment.Can comprise the pigment dyestuff of any kind basically according to tinting pigment of the present invention, for example organic black pigments and other organic coloring pigment comprise blue pigments, brown pigments, green pigment, veridian, white pigment, violet pigment, magenta pigment, red pigment, orange pigments or yellow ultramarine.Do not comprise charcoal blacks according to tinting pigment of the present invention.Suitable organic black pigments kind comprises nigrosine with perylene is black.The representative example of nigrosine comprises Pigment black 1.The representative example that perylene is black comprises Pigment black 31 and Pigment black 32.
And suitable classes of colored pigments comprises for example anthraquinone, phthalocyanine blue, phthalocyanine green, diazo pigment, monoazo pigment, pyranthrone, perylene, heterocyclic yellows, quinacridone, quinolone and quinolone (quinolonoquinolone) and (sulphur) indigo.The representative example of phthalocyanine blue comprises copper phthalocyanine blue and derivative (for example, pigment Blue 15 series) thereof.The representative example of phthalocyanine green comprises many chloros copper phthalocyanine green and derivative (for example, pigment Green 7 and pigment green 36) thereof.The representative example of quinacridone comprises pigment orange 48, pigment orange 49, pigment red 122, Pigment red 192, Pigment red 202, Pigment red 206, Pigment Red 207, Pigment red 209, pigment violet 19 and pigment violet 42.The representative example of anthraquinone comprises pigment red 43, Pigment red 194 ((Perinone) is red for purple cyclic ketones), pigment red 21 6 (the bromo pyranthrone is red) and Pigment red 226 (pyranthrone is red).The representative example of perylene comprises pigment red 123 (vermilion red), pigment red 149 (scarlet), Pigment red 179 (hestnut color), Pigment red 190 (red), pigment violet 19, Pigment red 189 (Huang Xianghong) and Pigment red 224.The representative example of thioindigo comprises pigment Red 86, pigment Red 87, pigment Red 88, Pigment red 181, Pigment red 198, pigment violet 36 and pigment violet 38.The representative example of heterocyclic yellows comprises Pigment Yellow 73 1, Pigment Yellow 73 3, pigment Yellow 12, pigment yellow 13, pigment Yellow 14, pigment yellow 17, Pigment Yellow 73 65, Pigment Yellow 73 73, Pigment Yellow 73 74, Pigment Yellow 73 151, Pigment Yellow 73 117, pigment Yellow 12 8 and pigment yellow 13 8.Such pigment can powder or cake form be commercially available from the many sources that comprise BASF Corporation, EngelhardCorporation, Sun Chemical Corporation, Clariant, Dianippon Inkand Chemicals (DIC).At Colour Index, the example of other suitable tinting pigment has been described among the 3rd edition (The Society of Dyersand Colourists, 1982).The mixture of certain different pigment can be used as the blend of independent pigment or comprises the pigment use of multiple tinting material.The preferred kind of pigment comprises phthalocyanine blue and quinacridone.
According to the required character of described pigment, described pigment can have various BET surface-area, and described BET surface-area is measured by nitrogen adsorption.Preferably, pigment has about 10m
2/ g～about 1500m
2/ g, 20m more preferably from about
2/ g～about 600m
2/ g and 50m most preferably from about
2/ g～about 300m
2The BET surface-area of/g.If the application for expectation can not easily obtain the surface-area expected, then those skilled in the art also are fully recognized that, if desired, described pigment can experience that conventional size reduces or crushing technology (for example ball milling or jet mill or supersound process) so that described pigment is decreased to less granularity.And described pigment can have various crystallite dimension as known in the art.For example, described pigment can have about 5nm～about 100nm, comprises the crystallite dimension of about 10nm～about 80nm and about 15nm～about 50nm.In addition, described pigment also can have various oil-absorption(number)s, and described oil-absorption(number) is the measuring of structure of described pigment.For example, described pigment can be has about 5～150mL/100g, comprises the organic coloring pigment of the oil-absorption(number) (described in ISO 787T5) of about 10～100mL/100g and about 20～80mL/100g.
Described pigment also can be and has used the oxygenant oxidation to introduce the pigment of ionic group and/or the Ionized group of energy from the teeth outwards.In addition, also can use the pigment that utilizes for example chlorination of other surface modifying method, sulfonation and sulfonylation preparation.
Described organic group is connected with described tinting pigment via at least one carbon atom of C-C singly-bound or two keys, and wherein said C-C singly-bound or two key are not the parts of aromatic systems.Can with organic compound reaction described organic group be connected with described tinting pigment by making tinting pigment with two keys of C-C or triple bond and at least one active group on this C-C pair of keys or at least one carbon atom of triple-linked.Gained comprises active group at least one at least one carbon atom at described C-C singly-bound or two keys through the pigment of modification.Usually preferred electrophilic active group.Suitable active group comprises for example acyl group, formyl radical, carboxyl, alkoxy carbonyl, aryloxycarbonyl, acyloxy carbonyl, cyano group, formamyl, alkyl-carbamoyl, aryl-amino-carbonyl, acyl amino formyl radical, alkyl sulphonyl, aryl sulfonyl, alkoxyl group alkylsulfonyl, aryloxy sulfonyl, alkyl sulphinyl, aryl sulfonyl kia, phosphono, alkoxyl group phosphono and aryloxy phosphono.Preferred active group comprises: carboxyl, alkoxy carbonyl, aryloxycarbonyl, acyloxy carbonyl, formamyl, alkyl-carbamoyl, aryl-amino-carbonyl and acyl amino formyl radical.
Preferred active group comprises-CO-R
5,-CHO ,-COOR
5,-COOH ,-CN ,-SO
2R
5, and-CO-X-CO-, wherein X is selected from O and N-R
5R
5Be selected from alkyl, functionalized alkyl, polymkeric substance, cyclic organic group, aryl and the Ar-Y of Y
nThe aryl that the Y of form is functionalized; Wherein n be 1～5 and Y be selected from-OH ,-OR ,-SH ,-SR ,-SO
3H ,-SO
3 -M
+,-SO
2R ,-B (OH)
2,-O (CH
2-CH
2-O)
m-H ,-COOH ,-COO
-M
+,-NH
2,-NR
2,-N ((CH
2-CH
2-O)
nH)
2,-CON ((CH
2-CH
2-O)
nH)
2, trialkoxysilyl, perfluoroalkyl, alkyl ,-NH
3 +Q
-,-NR
3 +Q
-,-SO
2-NR
2,-NO
2,-Cl ,-COR ,-COOR ,-NO
2,-SSR ,-SCN ,-CN ,-PO
3H
2, and-PO
3 -2M
+ 2M wherein
+Be alkalimetal ion or alkaline-earth metal ions, Q
-Be halide-ions, nitrate ion, carboxylic acid ion (for example acetate ion) or sulfate ion; M is 1～50, and R is selected from: H, alkyl, aryl, functionalized alkyl, functionalized aryl and polymkeric substance.For R and R
5Preferred polymers comprise polyamine, polyalkylene oxide, polyalkylene glycol, polyol, poly-(methyl) acrylate, protein, polyamino acid, polyureas, urethane, polyureas/carbamate, polyester, polyethers, polyvingl ether, polymeric amide, polyimide, polyolefine, polyolefine-acrylate, polystyrene (comprising vinylbenzene (methyl) acrylate copolymer), their salt and their derivative.
Another aspect of the invention is the manufacture method through the tinting pigment of modification of organic group with at least one connection.Described method comprises to be made tinting pigment and has two keys of C-C or the triple bond step with the organic compound reaction of at least one active group on the two keys of this C-C or at least one carbon atom of triple-linked.Reaction product comprises aforesaid tinting pigment with organic group of at least one connection.Can use any basically suitable, have an organic compound of two keys of C-C or triple bond and at least one active group on the two keys of this C-C or at least one carbon atom of triple-linked.Such organic compound generally can be described as alkynes (triple bond) derivative or alkene (two key) derivative.The alkynes derivative can be by formula R
1C ≡ CR
2Expression and alkene derivatives can be by formula R
1R
3C=CR
2R
4Expression.R
1For example can comprise-CO-R
5,-CHO ,-COOR
5,-COOH ,-CN and-SO
2R
5R
2, R
3, and R
4Can comprise R
1, H, alkyl or aryl.R
5Can be above-mentioned in those any one and can comprise alkyl, aryl or functionalized alkyl or functionalized aryl for example ω-carboxyalkyl, carboxyl aryl, HO
3The S-alkyl-, H
2The N-alkyl-, H
2N-SO
2-alkyl-, HO
3The S-aryl-, H
2The N-aryl-, H
2N-SO
2-aryl-and similar group.
Suitable organic compound also can comprise maleic anhydride and maleic acid derivatives.Maleic acid derivatives can be by formula C
4H
2O
2X represents that wherein X can comprise O and N-R
5R
5Can as above define.R
5Also can comprise aliphatic group, cyclic organic group or have the organic compound of aliphatic series part and circular part.R
5May further be replacement or unsubstituted, branching or nonbranched, perhaps comprise aliphatic group for example alkane group, olefin group, alcohol radical, ether, aldehyde radical, ketone group, hydroxy-acid group, ester group and alkyl.R
5Can comprise further that also ring compound (for example, alicyclic hydrocarbon is cycloalkyl or cycloalkenyl group for example), heterogeneous ring compound (for example, pyrrolidyl-, pyrrolinyl-, piperidyl or morpholinyl), aryl (for example phenyl, naphthyl or anthryl) or heteroaryl (for example, imidazolyl, pyrazolyl, pyridyl, thienyl, thiazolyl, furyl or indyl).
Preferred organic compound comprises maleic anhydride, toxilic acid, fumaric acid, acetylenedicarboxylic acid and their derivative.The preferred derivative of toxilic acid, fumaric acid and acetylenedicarboxylic acid comprises carboxylic acid, dicarboxylic acid, ester, acid amides and imide.Maleic anhydride is most preferred organic compound.
Find surprisingly that above-mentioned organic compound and organic coloring pigment react and described organic coloring pigment is carried out modification.More specifically describe as following (in an embodiment), can make the organic compound reaction of organic coloring pigment and capacity, make described tinting pigment to be dispersed in the water-bearing media.U.S. Patent No. 6,660,075 discloses the carbon black with above-mentioned organic compound reaction.Therefore organic coloring pigment has very different surface reaction site and surface reaction, and does not expect its and organic compound reaction same type the same with carbon black.
Above-mentioned tinting pigment through modification is reacted to form the pigment of polymer modification with nucleophilic polymer further.Can utilize any basically suitable nucleophilic polymer.Comprise or correctability is that the illustrative polymers that comprises nucleophile (nucleophile) is drawn together polyamine, polyalkylene oxide, polyalkylene glycol, polyol, poly-(methyl) acrylate, protein, polyamino acid, polyureas, urethane, polyureas/carbamate, polyester, polyethers, polyvingl ether, polymeric amide, polyimide, polyolefine, polyolefine-acrylate, polystyrene (for example vinylbenzene (methyl) acrylate copolymer), their salt, with their derivative.
Of the present inventionly can be used for multiple application, for example comprise plastics composite, moisture or non-aqueous ink, moisture or non-aqueous coating, rubber combination, paper compositions, toning agent and fabric composition through modified pigment.Specifically, these pigment can be used for aqueous composition, comprise for example automobile and industrial coating, paint, tackiness agent, latex and printing ink.Have been found that described pigment is the most useful in ink composite especially jetted ink.Therefore, the invention further relates to and comprise supporting agent and through the dispersion and the inkjet ink composition of modified pigment.Described supporting agent can be moisture or the on-aqueous liquid supporting agent, but is preferably the supporting agent that contains water.Therefore, described supporting agent is preferably moisture supporting agent, and described dispersion and inkjet ink composition are aqueous composition.More preferably, described supporting agent contain surpass 50% water and comprise water for example or water and with the miscible solvent of water such as the mixture of alcohol.
Can use minimum additional component (additive and/or solubility promoter) and procedure of processing to form according to inkjet ink composition of the present invention.Yet, can introduce suitable additive so that in the stability that keeps described composition, give the character of many expectations.For example, can add tensio-active agent and/or dispersion agent, wetting agent, dry promotor, permeate agent, biocide (biocide), tackiness agent and pH control agent and other additive as known in the art.The amount of special additive changes according to multiple factor, but is generally 0%～40%.
Can add dispersion agent (tensio-active agent and/or dispersion agent) with the colloidal stability of further enhancing composition or change printing ink and printing substrate for example printing paper or with the interaction of ink printing head.Various anionics, cationic and non-ionic dispersing agent can be used in combination with ink composite of the present invention, and these can be solid form or as the aqueous solution.
The representative example of anionic dispersing agent or tensio-active agent comprises; but be not limited to higher fatty acid salt; the senior alkyl dicarboxylate; the sulfuric acid of higher alcohols; senior alkyl sulfonate; alkylbenzene sulfonate; sulfonated alkyl naphathalene; naphthalenesulfonate (Na; K; Li; Ca etc.); the formalin polycondensate; condenses between higher fatty acid and the amino acid; dialkyl sulfosuccinic salt (dialkylsulfosuccinicacid ester salt); alkyl sulfosuccinate succinate (alkylsulfosuccinate); naphthenate; the alkyl ether carboxy acid salt; the peptide of acidylate; sulfonated; N-acryl N-methyltaurine; alkylether sulfonate; senior secondary alcohol ethoxy sulfate; polyoxyethylene alkylphenyl ether sulfate salt; single glycyl vitriol; alkyl ether phosphate salt and alkyl phosphate salt; alkyl phosphonate and diphosphonate comprise hydroxylation or aminating derivative.For example, the polymkeric substance and the multipolymer of styrene sulfonate, the naphthalenesulfonate (for example alkyl or alkoxyl group replace naphthalene derivatives), aldehyde derivatives (for example the unsubstituted alkyl aldehyde derivatives comprises formaldehyde, acetaldehyde and propionic aldehyde etc.), maleate and their mixture that do not replace and replace can be used as described anionic dispersing auxiliary.Salt comprises for example Na
+, Li
+, K
+, Cs
+, Rb
+, and replacement and unsubstituted ammonium cation.Specific examples includes, but are not limited to for example following Industrial products:
With
77 (National Starchand Chemical Co.);
D (Diamond Shamrock Chemicals Co.);
19 Hes
K (W.R.GraceCo.); With
SN (Rohm﹠amp; Haas).The representative example of cationic surfactant comprises aliphatic amine, quaternary ammonium salt, sulfonium salt, squama salt etc.
Can be used for the non-ionic dispersing agent in the jetted ink of the present invention or the representative example of tensio-active agent and comprise that the alkyne diol of fluorine derivative, organosilicon derivates, acrylic copolymer, Voranol EP 2001, polyoxyethylene alkyl phenyl ether, polyoxyethylene secondary alcohol ether, polyoxyethylene vinylbenzene ether, ethoxylation (for example can derive from Air Products's
420,
440 Hes
465), the Wool wax alcohols,ethoxylated derivative, the epoxyethane derivative of alkylphenol formalin condenses, the polyoxyethylene polyoxypropylene block polymer, the fatty acid ester of polyoxyethylene polyoxy-propylene polyoxyethylene compound, the glycol fatty acid ester of polyethylene oxide condensed type, glycerine monofatty ester, the fatty acid ester of polyglycerol, the fatty acid ester of propylene glycol, sucrose fatty ester, fatty acid alkyl amide, polyoxyethylene fatty acid acid amides and polyoxyethylene alkyl amine oxide compound.For example, can use the monoalkyl or the dialkyl phenol of ethoxylation, for example
CA and CO series material (Rhone-Poulenc Co.),
Series material (ICIAmericas, Inc.) and
Series material (Union Carbide Company).These nonionic surface active agent or dispersion agent can use separately or be used in combination with above-mentioned anionic and cationic dispersing agent.
Described dispersion agent also can be natural polymer or synthetic polymer dispersion agent.The specific examples of natural polymer dispersion agent comprises: protein, for example glue, gelatin, casein and albumin; Natural rubber, for example Sudan Gum-arabic and tragacanth gum; Glucoside, for example saponin; Lalgine and Lalgine derivative be propylene glycol alginate, trolamine alginates and ammonium alginate for example; And derivatived cellulose for example methylcellulose gum, carboxymethyl cellulose, Natvosol and ethyl hydroxylated cellulose.The specific examples of polymer dispersant (comprising synthetic polymer type dispersion agent) comprising: polyvinyl alcohol, for example from the Elvanols of DuPont, from the Celvoline of Celanese; Polyvinylpyrrolidone, for example from the Luvatec of BASF, from Kollidon and Plasdone and the PVP-K (Glide) of ISP; Acrylic acid or the like or methacrylic resin (usually writing " (methyl) acrylic acid or the like "), for example poly-(methyl) vinylformic acid (from the Ethacryl series of Lyondell, from the Alcosperse of Alco), vinylformic acid-(methyl) acrylonitrile copolymer, (methyl) potassium acrylate-(methyl) acrylonitrile copolymer, vinyl-acetic ester-(methyl) acrylate copolymer and (methyl) vinylformic acid-(methyl) acrylate copolymer; Styrene-propene acids or methacrylic resin, for example vinylbenzene-(methyl) acrylic copolymer is as from the Joncryl series of BASF, from the Carbomers of Noveon, vinylbenzene-(methyl) vinylformic acid-(methyl) acrylate copolymer is as the Joncryl polymkeric substance from BASF, styrene--(methyl) acrylic copolymer, styrene--(methyl) vinylformic acid-(methyl) acrylate copolymer; Styrene-maleic acid copolymer; Styrene-maleic anhydride copolymer is for example from the SMA polymkeric substance of Sartomer; Vinyl naphthalene-acrylic or methacrylic acid copolymer; Vinyl naphthalene-maleic acid; And vinyl acetate copolymer, for example vinyl-acetic ester-ethylene copolymer, vinyl-acetic ester-fatty acid vinyl ethylene copolymer, vinyl-acetic ester-maleate copolymer, vinyl-acetic ester-Ba Dousuan multipolymer and vinyl-acetic ester-acrylic copolymer; And their salt.From the Tego product of Degussa, from the Ethacryl product of Lyondell, from the Joncryl polymkeric substance of BASF, from the EFKA dispersion agent of Ciba and derive from the Disperbyk of BYK Chemie and the Byk dispersion agent in comprised polymkeric substance (for example listed above those), modification and the associated materials of the dispersion agent that can be used in the jetted ink and additive:.
Wetting agent and water-soluble organic compounds also can join in the inkjet ink composition of the present invention, particularly purpose and drying (dry promotor) and the crease-resistant character for paper infiltration (permeate agent) being provided, improving in order to prevent spray nozzle clogging.The specific examples of spendable wetting agent and other water-soluble organic compounds comprises: low molecular weight diols is ethylene glycol, glycol ether, triglycol, Tetraglycol 99 and dipropylene glycol for example; The dibasic alcohol that contains 2～about 40 carbon atoms of having an appointment, for example 1,3-pentanediol, 1,4-butyleneglycol, 1,5-pentanediol, 1,4-pentanediol, 1,6-hexylene glycol, 1,5-hexylene glycol, 2, and 6-hexylene glycol, neopentyl glycol (2,2-dimethyl-1, ammediol), 1, ammediol, 1,4-butyleneglycol, 1,5-pentanediol, 1,6-hexylene glycol, 1,2, the reaction product of 6-hexanetriol, poly-(ethene-copolymerization-propylene) glycol etc. and they and epoxy alkane (comprise oxyethane, comprise oxyethane and propylene oxide); Contain the trivalent alcohol derivative of 3～about 40 carbon atoms of having an appointment, comprise glycerine, TriMethylolPropane(TMP), 1,3,5-penta triol, 1,2, the reaction product of 6-hexanetriol etc. and they and epoxy alkane (comprising oxyethane, propylene oxide and its mixture); The reaction product of neopentyl glycol, (2) etc. and they and epoxy alkane, described epoxy alkane comprises the oxyethane of any required molar ratio and propylene oxide has various molecular weight with formation material; Thiodiglycol; Tetramethylolmethane and lower alcohol be ethanol, propyl alcohol, Virahol, propyl carbinol, sec-butyl alcohol and the trimethyl carbinol, 2-propine-1-alcohol (propargyl alcohol), 2-butylene-1-alcohol, 3-butene-2-alcohol, 3-butyne-2-alcohol and ring propyl alcohol for example; Acid amides, for example dimethyl formamide and N,N-DIMETHYLACETAMIDE; Ketone or keto-alcohol, for example acetone and diacetone alcohol; Ether, for example tetrahydrofuran (THF) is with diox; Cellosolve, for example ethylene glycol monomethyl ether and ethylene glycol monoethyl ether, triglycol list first (or single second) ether; Trivalin SF, for example diethylene glycol monomethyl ether, diethylene glycol monoethyl ether and diethylene glycol monobutyl ether; Lactan, for example 2-Pyrrolidone, N-N-methyl-2-2-pyrrolidone N-and ε-Ji Neixianan; Urea and urea derivatives; Inner salt is trimethyl-glycine etc. for example; The sulfo-of above-mentioned materials (sulphur) derivative comprises the 1-butyl sulfhydryl; Tert.-butyl mercaptan 1-methyl isophthalic acid-propylmercaptan, 2-methyl isophthalic acid-propylmercaptan; 2-methyl-2-propylmercaptan; Sulfo-ring propyl alcohol, THIOGLYCOL, sulfo-glycol ether, trithio-or dithio-glycol ether etc.; Hydroxyamide derivatives comprises acetyl ethanolamine, ethanoyl Propanolamine, propyl group carboxyl thanomin, propyl group carboxyl Propanolamine etc.; The reaction product of above-mentioned materials and epoxy alkane; And their mixture.Other example comprises: carbohydrate, for example maltose alcohol, Sorbitol Powder, glucono-lactone and maltose; Polyvalent alcohol, for example TriMethylolPropane(TMP) and trimethylolethane; The N-N-methyl-2-2-pyrrolidone N-; 1,3-dimethyl-2-imidazolidone; The sulfoxide derivant that contains 2～about 40 carbon atoms of having an appointment comprises dialkyl sulphoxide (symmetry and asymmetric sulfoxide) for example dimethyl sulfoxide (DMSO), methyl-sulfinyl-ethane, alkyl phenyl sulfoxide etc.; With the sulfone derivatives that contains 2～about 40 carbon atoms of having an appointment (symmetry and asymmetric sulfone), for example dimethyl sulfone, methylethyl sulfone, tetramethylene sulfone (tetramethylene sulfone, it is a cyclic sulfones), dialkyl sulfone, alkyl phenyl sulfone, dimethyl sulfone, methylethyl sulfone, diethyl sulfone, ethyl propyl sulfone, methyl phenyl sulfone, methyl sulfolane, dimethylsulfolane etc.Such material can be used singly or in combination.
Also biocide and/or mould inhibitor (fungicide) can be joined in the inkjet ink composition of the present invention.Biocide is for preventing that bacterial growth from being important, because bacterium is bigger and can cause stopping up and other printing issues than printing ink nozzle usually.The example of useful biocide includes, but are not limited to benzoate or sorbate, and isothiazolinone.
Also can use with the viscosity of regulating described composition with inkjet ink composition of the present invention various polymer type adhesives and other required character is provided.Suitable polymers type tackiness agent comprises, but be not limited to: water-soluble polymers and multipolymer, Sudan Gum-arabic for example, polyacrylate, poly-methyl acrylate, polyvinyl alcohol is (from the Elvanols of DuPont, Celvoline from Celanese), hydroxyl tacryl element, Natvosol, polyvinylpyrrolidone (for example, Luvatec from BASF, Kollidon and Plasdone from ISP, and PVP-K (G1ide)), polyvingl ether, starch, polysaccharide, use or do not use oxyethane and propylene oxide to carry out the deutero-polymine, or the like, described polymine comprises
Series (DKS International),
Series (Huntsman).The other example of water-soluble polymeric compounds comprises above-mentioned various dispersion agents or tensio-active agent, comprise that styrene-propene acid copolymer for example is (for example, from the Joncryl series of BASF, Carbomers from Noveon), styrene-propene acid-alkyl acrylate terpolymer, vinylbenzene-Sipacril 2739OF (for example from BASF Joncryl series), styrene-maleic acid copolymer (for example from Sartomer SMA polymkeric substance), styrene-maleic acid-alkyl acrylate terpolymer, vinylbenzene-methacrylic acid-alkyl acrylate terpolymer, styrene-maleic acid half ester multipolymer, vinyl naphthalene-acrylic copolymer, Lalgine, polyacrylic acid or their salt and their derivative.In addition, described tackiness agent can dispersion or interpolation of latex form or existence.For example, described polymer type adhesive can be the latex of acrylate or alkylmethacrylate polymer (for example, from the NeoCryl material of NSMNeoresins, from AC and the AS polymkeric substance of Alberdingk-Boley) or can be can water-dispersion urethane (for example from Alberdingk-Boley ABU) or polyester (for example from Eastman Chemical AQ polymkeric substance).The polymkeric substance that can be used for the tackiness agent in the jetted ink (for example listed above those), modification and associated materials in from the Ethacryl product of Lyondell, from the Joncryl polymkeric substance of BASF, from the AC of the NeoCryl material of NSM Neoresins and Alberdingk-Boley and AS polymkeric substance, have been comprised.
Also can use the various additives of the pH that is used to control or regulate inkjet ink composition of the present invention.The example of suitable pH regulator agent comprises various amine, for example diethanolamine and trolamine and various hydroxide reagent.Hydroxide reagent is any OH that comprises
-Ionic reagent for example has the salt of hydroxide radical counter ion.Example comprises sodium hydroxide, potassium hydroxide, lithium hydroxide, ammonium hydroxide and tetramethyl ammonium hydroxide.Also can use the mixture of other hydroxide salt and hydroxide reagent.In addition, also can use and in water-bearing media, produce OH
-Other alkaline reagents of ionic.Example comprises: carbonate, for example yellow soda ash; Supercarbonate, for example sodium bicarbonate; And alkoxide, for example sodium methylate and sodium ethylate.Also can add buffer reagent.
In addition, inkjet ink composition of the present invention can further be introduced conventional dyestuff to change color balance and to regulate optical density(OD).Such dyestuff comprises: food dye; FD﹠amp; The C dyestuff; The acid type dyestuff; Substantive dyestuff; Reactive dyestuffs; The derivative of phthalocyanine sulfonic acid comprises sodium salt, ammonium salt, sylvite, lithium salts of CuPc derivative, phthalocyanine sulfonic acid etc.
Described inkjet ink composition can use for example above-mentioned method that is used for those methods of modified pigment of the present invention to carry out purifying and/or classification.Also can use optional counter ion exchange step.Thereby, can remove undesirable impurity or unwanted macrobead have good overall properties with manufacturing printing ink.
The present invention will further illustrate by the following embodiment that is intended to purely the present invention is carried out example.
Embodiment
Embodiment 1
Preparation 10.3 gram pigment Blue 15s: the mixture and the use rotor-stator of 4 (can derive from Sun Chemicals, carry out oven drying by filter cake), 2.1 gram maleic anhydrides and 100 milliliters of tetrahydrofuran (THF)s mixed 10 minutes.Then described mixture is evaporated until drying.Solids is scraped and descends to heat 6 hours at 180 ℃ from flask.After being cooled to room temperature, by under 0 ℃ in Misonix 3000 ultra-sonic generators that use little tip (microtip) with 5.5 power setting and open 8 seconds, close 2 seconds pulse cycle supersound process 20 minutes and described solids be dispersed among 50 milliliters of 1.0N KOH.After supersound process, do not observe (passing through visual inspection) particle and from suspension, settle.Described dispersion sedimentation not yet after 24 hours.Then before measuring granularity with described dispersion supersound process 20 minutes (being provided with identical) again.Use
Particle-size analyzer dynamic light scattering device measuring obtains (volume weighted) mean particle size with the volume balance of 422 nanometers.By using SpectrumMembrane (1050cm
2) and peristaltic pump carry out diafiltration and further described dispersion carried out purifying with the deionized water of 10 times of volumes.After three days, record the mean particle size with volume balance of 556 nanometers, this shows that in three days described particle is not significantly grown and the aqueous dispersion that comprises through modified pigment is stable basically.Use Brookhaven Zeta Plus to record the zeta-potential of-42 microvolts, this shows on institute's dispersed particles and has strong negative charge.Measured zeta-potential shows that further described dispersion is stable basically.
Embodiment 2
Preparation 46 gram pigment Blue 15s: the mixture and the use rotor-stator of 4 (can derive from Sun Chemicals, carry out oven drying by filter cake), 9.2 gram maleic anhydrides and 400 milliliters of tetrahydrofuran (THF)s mixed 10 minutes.Then described mixture is evaporated until drying.Solids is scraped and descends to heat 6 hours at 180 ℃ from flask, be cooled to room temperature.Described solids is used for embodiment 3 and 6 as more specifically described as the following like that.
Embodiment 3
The preparation 5 the gram embodiment 2 in the preparation solidss and 60 the gram quadrols mixture and with it in 0 ℃ of following supersound process 40 minutes (carrying out ultrasonic) according to program described in the embodiment 1.Use
Particle-size analyzer records the mean particle size with the volume balance of 840 nanometers.Described size-grade distribution is bimodal, has the peak in about 400 nanometers and 1500 nanometers.
Embodiment 4
Use semicontinuous fed technology to prepare the mixture of methacrylic acid/methyl methacrylate/benzyl methacrylate (25% methacrylic acid, 70% butyl acrylate, 5% benzyl methacrylate) with 50% solids concentration in 50/50 blend of butanols and isobutyl acetate.Join dodecyl mercaptans (is 2.5% based on described monomer feed) and butoxy acetic acid ethyl ester (is 3% based on described monomer feed) described in the blended monomer.Temperature is being remained under 85～95 ℃ the situation, with 170 minutes periods described mixture being fed in the solvent.Benzoyl peroxide (is 1% based on described monomer feed) is dissolved in small amount of N-methyl-2-pyrrolidone and in this identical period, adds as common charging.After finishing the benzoyl peroxide charging, kept this temperature of reaction 1 hour.In end in this 1 hour, add benzoyl peroxide with another equal portions that benzoyl peroxide equates first time.Be dissolved in then in the tetrahydrofuran (THF) (solids with about 10～20% is dissolved in the tetrahydrofuran (THF)) and collect described polymkeric substance by precipitation in hexane for twice.Recording the limiting viscosity of described polymkeric substance in tetrahydrofuran (THF) is that 0.09dL/g and acid number are 145 milligrams of KOH/ gram polymkeric substance.
Embodiment 5
Anhydrous N-Methyl pyrrolidone (180 gram) is fed in the 500 milliliter of three neck round-bottomed flask that is equipped with bull stick (spin bar), condenser and nitrogen inlet.Under agitation, adding 20 (20) restrains and it is dissolved in the described N-Methyl pyrrolidone.Use constant temperature oil bath that the content of described flask is heated to 70 ℃.Quadrol (0.24 gram) is added in this polymers soln that is stirring in a charging.After 5 minutes, 1M solution 4.96 grams of dicyclohexylcarbodiimide in methylene dichloride are joined in the described reactor in the single charging.Be reflected at 70 ℃ and kept 3 hours down, be cooled to envrionment temperature, and stirred in addition 14 hours.Form a spot of white depositions and it is removed by vacuum filtration.Use resulting polymers solution and be not further purified.
Embodiment 6
With the solids of the preparation in polymer-modified (2 gram polymkeric substance in 10 milliliters of N-Methyl pyrrolidone), 2 gram embodiment 2 of embodiment 5 and 5 milliliters of N-Methyl pyrrolidone combinations and 0 ℃ of following supersound process (as described in the embodiment 1) 30 minutes.Then described mixture is heated in baking oven 60 ℃ three days.When three days finish, described sample poured among 200 milliliters the 100mM NaOH and supersound process 7 minutes.Use
Particle-size analyzer records the mean particle size with the volume balance of 200 nanometers.In the 50mM of 5 times of volumes NaCl, in the deionized water of 10 times of volumes, described dispersion is carried out diafiltration then.Recording the final mean particle size with the volume balance is 311 nanometers, and in 200 nanometers the peak is arranged in distribution.
The foregoing description that has presented the preferred embodiment for the present invention is to describe and to describe.It is not intended to for limit or limit the invention to disclosed exact form.Improvement and modification are feasible according to above instruction, perhaps can be known by practice of the present invention.Embodiment is selected and described explaining principle of the present invention and practical application thereof, so that make those skilled in the art utilize the present invention with the various modification of the concrete application that is suitable for expecting in various embodiments neutralizations.Being intended that scope of the present invention should be limited by claims and Equivalent thereof.
Claims (23)
1. through the tinting pigment of modification, comprise:
Tinting pigment; With
The organic group of at least one connection;
Wherein said organic group is connected with described tinting pigment via at least one carbon atom of C-C singly-bound or two keys, wherein said C-C singly-bound or two key are not the parts of aromatic systems, and wherein said organic group further comprises at least one active group at least one carbon atom of described C-C singly-bound or two keys.
2. the tinting pigment through modification of claim 1, wherein said active group comprises electron-withdrawing group.
3. the tinting pigment through modification of claim 1, wherein said active group is carboxyl, alkoxy carbonyl, aryloxycarbonyl, acyloxy carbonyl, formamyl, alkyl-carbamoyl, aryl-amino-carbonyl or acyl amino formyl radical.
4. the tinting pigment through modification of claim 1, wherein said active group is selected from-CO-R
5,-CHO ,-COOR
5,-COOH ,-CN ,-SO
2R
5, and-CO-X-CO-, wherein X is selected from O and N-R
5And R wherein
5Be selected from alkyl, functionalized alkyl, polymkeric substance, cyclic organic group, aryl and the Ar-Y of Y
nThe aryl that the Y of form is functionalized; Wherein Y be selected from-OH ,-OR ,-SH ,-SR ,-SO
3H ,-SO
3 -M
+,-SO
2R ,-B (OH)
2,-O (CH
2-CH
2-O)
m-H ,-COOH ,-COO
-M
+,-NH
2,-NR
2,-N ((CH
2-CH
2-O)
nH)
2,-CON ((CH
2-CH
2-O)
nH)
2, trialkoxysilyl, perfluoroalkyl, alkyl ,-NH
3 +Q
-,-NR
3 +Q
-,-SO
2-NR
2,-NO
2,-Cl ,-COR ,-COOR ,-NO
2,-SSR ,-SCN ,-CN ,-PO
3H
2, and-PO
3 -2M
+ 2M is alkalimetal ion or alkaline-earth metal ions, Q
-Be halide-ions, nitrate ion, carboxylic acid ion or sulfate ion; M is 1～50; And n is 1～5.
5. the tinting pigment through modification of claim 4, wherein said polymkeric substance are polyamine, polyalkylene oxide, polyalkylene glycol, polyol, poly-(methyl) acrylate, protein, polyamino acid, polyureas, urethane, polyureas/carbamate, polyester, polyethers, polyvingl ether, polymeric amide, polyimide, polyolefine, polyolefine-acrylate, polystyrene, vinylbenzene (methyl) acrylate copolymer, their salt or their derivative.
6. the tinting pigment through modification of claim 1, wherein said tinting pigment is black pigment, blue pigments, brown pigments, green pigment, veridian, white pigment, violet pigment, magenta pigment, red pigment, orange pigments or yellow ultramarine, perhaps their mixture.
7. the tinting pigment through modification of claim 1, wherein said tinting pigment are that nigrosine, perylene is black, anthraquinone, phthalocyanine blue, phthalocyanine green, diazo pigment, monoazo pigment, pyranthrone, heterocyclic yellows, quinacridone, quinolone and quinolone, (sulphur) indigo or their mixture.
8. the tinting pigment through modification of claim 1, wherein said tinting pigment is phthalocyanine blue, quinacridone or their mixture.
9. the tinting pigment through modification of claim 1, wherein said organic group is connected with described tinting pigment with the amount that is enough to improve through the dispersiveness of tinting pigment in water-bearing media of surface modification.
10. through the tinting pigment of modification, it comprises the reaction product through the tinting pigment of modification of nucleophilic polymer and claim 1.
11. the tinting pigment through modification of claim 10, wherein said nucleophilic polymer comprises or is modified as and comprise nucleophile that wherein said nucleophilic polymer is selected from polyamine, polyalkylene oxide, polyalkylene glycol, polyol, poly-(methyl) acrylate, protein, polyamino acid, polyureas, urethane, polyureas/carbamate, polyester, polyethers, polyvingl ether, polymeric amide, polyimide, polyolefine, polyolefine-acrylate, polystyrene, vinylbenzene (methyl) acrylate copolymer, their salt and their derivative.
12., comprise the reaction product of following material through the tinting pigment of modification:
Tinting pigment; With
At least a organic compound that comprises two keys of C-C or triple bond and at least one active group on the two keys of described C-C or at least one carbon atom of triple-linked,
Wherein said reaction product comprises the organic group that at least one carbon atom via C-C singly-bound or two keys is connected with described tinting pigment, wherein said C-C singly-bound or two key are not the parts of aromatic systems, and wherein said organic group further is included in the active group at least one carbon atoms of described C-C singly-bound or two keys.
13. the tinting pigment through modification of claim 12, wherein said organic compound is maleic anhydride, toxilic acid, acetylenedicarboxylic acid, fumaric acid, the perhaps derivative of toxilic acid, acetylenedicarboxylic acid or fumaric acid, wherein said derivative is carboxylic acid, dicarboxylic acid, ester, acid amides or imide.
14. the tinting pigment through modification of claim 12, wherein said organic compound is a maleic anhydride.
15. the tinting pigment through modification of claim 12, wherein said active group are carboxyl, alkoxy carbonyl, aryloxycarbonyl, acyloxy carbonyl, formamyl, alkyl-carbamoyl, aryl-amino-carbonyl or acyl amino formyl radical.
16. that the tinting pigment through modification of claim 12, wherein said tinting pigment are nigrosine, perylene is black, anthraquinone, phthalocyanine blue, phthalocyanine green, diazo pigment, monoazo pigment, pyranthrone, heterocyclic yellows, quinacridone, quinolone and quinolone, (sulphur) indigo or their mixture.
17. the tinting pigment through modification of claim 12, wherein said tinting pigment are phthalocyanine blue, quinacridone or their mixture.
18. dispersion comprises:
Liquid carrier; With
Be dispersed in the tinting pigment in the described liquid carrier through modification,
Wherein said tinting pigment through modification comprises the organic group that tinting pigment is connected with at least one, described organic group is connected with described tinting pigment via at least one carbon atom of C-C singly-bound or two keys, wherein said C-C singly-bound or two key are not the parts of aromatic systems, and wherein said organic group further comprises at least one active group at least one carbon atom of described C-C singly-bound or two keys.
19. the dispersion of claim 18, wherein said liquid carrier are liquid, aqueous supporting agent.
20. the dispersion of claim 18, wherein said liquid carrier are the on-aqueous liquid supporting agent.
21. jetted ink comprises:
Liquid carrier; With
Be dispersed in the tinting pigment in the described liquid carrier through modification,
Wherein said tinting pigment through modification comprises the organic group that tinting pigment is connected with at least one, described organic group is connected with described tinting pigment via at least one carbon atom of C-C singly-bound or two keys, wherein said C-C singly-bound or two key are not the parts of aromatic systems, and wherein said organic group further comprises at least one active group at least one carbon atom of described C-C singly-bound or two keys.
22. the jetted ink of claim 21, wherein said liquid carrier are liquid, aqueous supporting agent.
23. the jetted ink of claim 21, wherein said liquid carrier are the on-aqueous liquid supporting agent.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/973,687 US20090095200A1 (en) | 2007-10-10 | 2007-10-10 | Modified colored pigments |
| US11/973,687 | 2007-10-10 | ||
| PCT/US2008/011573 WO2009048564A2 (en) | 2007-10-10 | 2008-10-08 | Modified colored pigments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101821341A true CN101821341A (en) | 2010-09-01 |
Family
ID=40532933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200880110951A Pending CN101821341A (en) | 2007-10-10 | 2008-10-08 | Tinting pigment through modification |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US20090095200A1 (en) |
| EP (1) | EP2203525A2 (en) |
| CN (1) | CN101821341A (en) |
| WO (1) | WO2009048564A2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845247A (en) * | 2009-03-25 | 2010-09-29 | 理想科学工业株式会社 | Non-aqueous pigment ink |
| CN109610187A (en) * | 2018-12-29 | 2019-04-12 | 福建宝利特科技股份有限公司 | Leather heat reflection colorant |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101891968B (en) * | 2010-05-25 | 2016-04-13 | 大连理工大学 | Low-polymerization-degree polycarboxylic dye |
| US9238736B2 (en) * | 2010-10-15 | 2016-01-19 | Cabot Corporation | Surface modified organic black pigments, surface modified carbon blacks, pigment mixtures using them, and low dielectric black dispersions, coatings, films, black matrices, and devices containing same |
| US8986842B2 (en) | 2011-05-24 | 2015-03-24 | Ecole Polytechnique Federale De Lausanne (Epfl) | Color conversion films comprising polymer-substituted organic fluorescent dyes |
| NL2011151C2 (en) | 2012-07-13 | 2015-03-24 | Cabot Corp | High structure carbon blacks. |
| BR112015021129A2 (en) | 2013-03-05 | 2017-07-18 | Cabot Corp | aqueous pigment dispersions |
| US20140267515A1 (en) | 2013-03-12 | 2014-09-18 | Cabot Corporation | Aqueous dispersions comprising nanocrystalline cellulose, and compositions for commercial inkjet printing |
| US9920209B2 (en) | 2014-10-14 | 2018-03-20 | Cabot Corporation | Aqueous inkjet ink compositions |
| WO2016187059A1 (en) | 2015-05-15 | 2016-11-24 | Cabot Corporation | Amphoteric polymers and use in inkjet ink compositions |
| WO2017087635A1 (en) | 2015-11-18 | 2017-05-26 | Cabot Corporation | Inkjet ink compositions |
| CN109923182A (en) | 2016-10-31 | 2019-06-21 | 卡博特公司 | Polymer for ink jet ink composition |
| WO2019051021A1 (en) | 2017-09-07 | 2019-03-14 | Cabot Corporation | Inkjet ink compositions |
| EP3622111B1 (en) | 2017-10-18 | 2021-05-26 | Hewlett-Packard Development Company, L.P. | Printing on a textile |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5914806A (en) * | 1998-02-11 | 1999-06-22 | International Business Machines Corporation | Stable electrophoretic particles for displays |
| US6336965B1 (en) * | 1998-04-03 | 2002-01-08 | Cabot Corporation | Modified pigments having improved dispersing properties |
| US20020096089A1 (en) * | 2000-03-16 | 2002-07-25 | Klaus Bergemann | Carbon Black |
| WO2003008509A1 (en) * | 2001-07-19 | 2003-01-30 | Cabot Corporation | Ink compositions comprising modified colored pigments and methods for preparing the same |
| US20050066856A1 (en) * | 2003-09-26 | 2005-03-31 | Samsung Electronics | Process for preparing self-dispersible coloring agent using lewis acids and ink composition comprising the coloring agent |
| US20060132568A1 (en) * | 2004-08-27 | 2006-06-22 | Canon Kabushiki Kaisha | Aqueous ink, ink jet recording method, ink cartridge, recording unit, ink jet recording apparatus and image forming method |
| US20060155008A1 (en) * | 2001-08-27 | 2006-07-13 | Seiko Epson Corporation | Microencapsulated pigment, production process therefor, aqueous dispersion, and ink jet recording ink |
| WO2007053564A2 (en) * | 2005-10-31 | 2007-05-10 | Cabot Corporation | Modified colorants and inkjet ink compositions comprising modified colorants |
| WO2008027405A2 (en) * | 2006-08-28 | 2008-03-06 | Cabot Corporation | Modified colorants with aliphatic poly-acid groups |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0904327B1 (en) * | 1996-06-14 | 2001-08-22 | Cabot Corporation | Modified colored pigments and ink jet inks containing them |
-
2007
- 2007-10-10 US US11/973,687 patent/US20090095200A1/en not_active Abandoned
-
2008
- 2008-10-08 CN CN200880110951A patent/CN101821341A/en active Pending
- 2008-10-08 WO PCT/US2008/011573 patent/WO2009048564A2/en active Application Filing
- 2008-10-08 EP EP08837512A patent/EP2203525A2/en not_active Withdrawn
-
2012
- 2012-07-25 US US13/557,697 patent/US20120285347A1/en not_active Abandoned
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5914806A (en) * | 1998-02-11 | 1999-06-22 | International Business Machines Corporation | Stable electrophoretic particles for displays |
| US6336965B1 (en) * | 1998-04-03 | 2002-01-08 | Cabot Corporation | Modified pigments having improved dispersing properties |
| US20020096089A1 (en) * | 2000-03-16 | 2002-07-25 | Klaus Bergemann | Carbon Black |
| WO2003008509A1 (en) * | 2001-07-19 | 2003-01-30 | Cabot Corporation | Ink compositions comprising modified colored pigments and methods for preparing the same |
| US20060155008A1 (en) * | 2001-08-27 | 2006-07-13 | Seiko Epson Corporation | Microencapsulated pigment, production process therefor, aqueous dispersion, and ink jet recording ink |
| US20050066856A1 (en) * | 2003-09-26 | 2005-03-31 | Samsung Electronics | Process for preparing self-dispersible coloring agent using lewis acids and ink composition comprising the coloring agent |
| US20060132568A1 (en) * | 2004-08-27 | 2006-06-22 | Canon Kabushiki Kaisha | Aqueous ink, ink jet recording method, ink cartridge, recording unit, ink jet recording apparatus and image forming method |
| WO2007053564A2 (en) * | 2005-10-31 | 2007-05-10 | Cabot Corporation | Modified colorants and inkjet ink compositions comprising modified colorants |
| WO2007053563A2 (en) * | 2005-10-31 | 2007-05-10 | Cabot Corporation | Modified colorants and inkjet ink compositions comprising modified colorants |
| WO2008027405A2 (en) * | 2006-08-28 | 2008-03-06 | Cabot Corporation | Modified colorants with aliphatic poly-acid groups |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845247A (en) * | 2009-03-25 | 2010-09-29 | 理想科学工业株式会社 | Non-aqueous pigment ink |
| CN101845247B (en) * | 2009-03-25 | 2013-07-10 | 理想科学工业株式会社 | Non-aqueous pigment ink |
| CN109610187A (en) * | 2018-12-29 | 2019-04-12 | 福建宝利特科技股份有限公司 | Leather heat reflection colorant |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2203525A2 (en) | 2010-07-07 |
| WO2009048564A3 (en) | 2010-04-15 |
| US20120285347A1 (en) | 2012-11-15 |
| WO2009048564A2 (en) | 2009-04-16 |
| US20090095200A1 (en) | 2009-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101821341A (en) | Tinting pigment through modification | |
| CN101970586B (en) | Modified pigments having reduced phosphate release, and dispersions and inkjet ink compositions therefrom | |
| CN101291996B (en) | Process for preparing modified pigments | |
| CN101351509B (en) | Modified colorants and inkjet ink compositions comprising modified colorants | |
| JP2011506635A (en) | Method for preparing pigment composition | |
| CN104619788B (en) | Super-normal structure black | |
| TWI415908B (en) | Manufacturing method of aqueous pigment dispersion and ink for ink-jet recording | |
| JP4138882B2 (en) | Colored pigment and aqueous composition containing the same | |
| CN101410468B (en) | Inkjet ink compositions comprising polymeric dispersants having attached chromophore groups | |
| JP2002538260A (en) | Preparation method of colored pigment | |
| JP2010516860A (en) | Method for producing modified pigments | |
| JP2004531591A (en) | Composition for ink containing salt having polyvalent ion | |
| JP2006045506A (en) | Polymer binder for inkjet ink | |
| US8362138B2 (en) | Water-insoluble colorant dispersion and production method thereof, and recording liquid, printed article, image-forming method and image-forming apparatus using the same | |
| CN102272248B (en) | Water-based ink for ink-jet printing | |
| CN101675130A (en) | The inkjet ink composition that comprises multiple modified pigment | |
| CN101528865B (en) | Modified colorants with aliphatic poly-acid groups | |
| TW200418936A (en) | Inkjet ink compositions | |
| JP7318278B2 (en) | Aqueous pigment dispersion and method for producing the same | |
| US20090018258A1 (en) | Inkjet ink compositions comprising polymer modified pigments and methods of preparing the same | |
| JP2008063580A (en) | Coloring agent for color filter | |
| EP4438687A1 (en) | Inkjet printing ink and method for producing printed matter | |
| JP4730573B2 (en) | Water-based ink composition for coating | |
| JP2006182943A (en) | Aqueous pigment liquid composition | |
| KR20100114423A (en) | Copolymer, methods for producing the same, and aqueous pigment compositions comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20100901 |